Salts of methylene citryl salicylic acid.



' UNITED sra'rns earrnrrr OFFICE.

RUnoLPi-I BEBENDEs AND Jtaenx CALLSEX, or ELBERFELD, GERMANY, ASSIGNORS TO FARBEXFABRIKEN roan. FRIEDR. BAYER & to, or ELBERFELD, GERMANY, A CORPORATION or GERMANY.

Specification of Letters Patent.

Patented June 25, 190?.

Application filed September 11, 1906. Renewed M21374, 1907. Serial No. 371,819.

To all whom it may concern:

Be it known that we, RUDOLPH BEREXDES and Jt'incnx OALLSEX, doctors of philosophy, chemists, citizen of the German Empire. residing at Elberfeld, Germany, Kingdom of Prussia, have invented new and useful Improvements in Salts of Methylene Citryl Salicylic Acid, of which the following is specification.

1 Our application Serial Number. 328055 filedJuly 27, 1906, relates to the new methylene citryl salicylic acid which exhibits valuable therapeutic properties. We have now found that this acid forms salts which have substantially the same ellect. These salts are not known up till now and are formed according to the known methods of forming salts e. g. by the action of bases upon the acid.

Two series of salts, namely acid and. neutral salts may be obtained. They are solid compounds winch yield the methylene citryl salicylic acid when treated with a mineral acid.

increased. The mass of the reaction is then allowed to stand for some time- The sodium salt is isolated by filtration, washed with ether and dried at moderate temperature.

The neutral sodium salt of methylene citryl salicylic acid having probably the formula:

CH2.COO.Ct-Hi.COONa 000/ CH.COO.C6Hi.COONa is after being dried, a White crystalline powder of neutral reaction having merely a slightly salty taste; It is readily soluble in water and insoluble in ether and benzene and yields the free methylene citryl salicylic acid by addition Of'llVClIOClllOIlC acid to its aqueous solution. peutic properties 6. g. as a medicine for rheumatism, an average dose being about one gram.

Example II. 444 parts of methylene citryl salicylic acid are stirred up with 500 parts of alcohol to a paste and 197 parts of barium carbonate are gradually added to this paste. The barium salt of methylene citryl salicylic acid is then isolate'das described in Exampl'el. It is a white crystalline powder soluble in cold and readily soluble in hot water.

Example III. 444 parts of methylene citryl salicylic acid are stirredup with a 50% alcohol to a paste and 148 parts of lithium carbonate are gradually added to this paste. The resulting solution is filtered, if necessary, and the lithium salt is isolated by the addition of alcohol and ether. It is a white crystalline powder soluble in water with neutral solution.

The process is carried out in an analogous manner for preparing other salts, such as the potassium salt, the ammonium salt, the hexamethylentetramin salt, or the like.

Having now described our invention and in what manner the same is to be performed, what we claim is 1. The herein described new salts of methylene citryl salicylic acid obtainable by It possesses valuable therathe action of bases u on methylene cit-ryl salicylic acid, being solid compounds yielding the free methylene citryl salicylic acid when treated with mineral acids; and exhibiting valuable therapeutic properties, substantially as described.

2. The herein-described new neutral so dium salt of methylene citryl salicylic acid, obtainable by the action of sodium b1carbon- Iateiipon methylene citryl salicylic acid, be-

ing a white crystalline powder readily Solo.

ble Water with a. neutral reaction, insolu set our hands in. i-ne firesence of two subscribble 1n ether and benzene; methylene citryi 'mg witnesses. salicyhc acid being regenerated by the addi- RUDGLPH BERENDES [t S 1 tion of hydrochloric acid to the aqueous s0- T 5 lution; and exhibiting valuablejhera-peutic TURGEIE CALLSENY properties, substantially as hersmbefore de- Vfittiessesf scrlbed. OTTO KGNIG,

In tes timony whereof We have hereuntd OTTO BUSCE. 

